Love it!
I think there is room to be witty with the document names. I get the feeling of nostalgia for summer and the outdoors, maybe incorporate that into the pictures? Rather than "picture 3" etc.
Overall I think it is sweet! $5

I like this design a lot. The icons seem somewhat disconnected from your excellent illustration because they don't cast shadows like the figure does. With a little tweaking this will definitely be a $5